Skip to main content
. Author manuscript; available in PMC: 2013 Mar 21.
Published in final edited form as: J Am Chem Soc. 2012 Mar 5;134(11):5131–5137. doi: 10.1021/ja209390d

Table 4.

Substrate scope of the tandem Friedel–Crafts conjugate addition/asymmetric protonation.a

graphic file with name nihms361777u4.jpg
entry
graphic file with name nihms361777t11.jpg
1) 76% yield, 93% ee
graphic file with name nihms361777t12.jpg
2) R = Me (7d) 63% yield, 85% ee
3) R = allyl (7e) 68% yield, 85% ee
graphic file with name nihms361777t13.jpg
4) 4-Me (7f): 88% yield, 96% ee
5) 5-Me (7g): 83% yield, 95% ee
6) 6-Me (7h): 80% yield, 89% ee
7) 7-Me (7i): 94% yield, 94% ee
graphic file with name nihms361777t14.jpg
7j
8) 85% yield, 91% ee
graphic file with name nihms361777t15.jpg
7k
9)b 60% yield, 93% ee
graphic file with name nihms361777t16.jpg
7l
10)b 63% yield, 92% ee
graphic file with name nihms361777t17.jpg
11) 4-Me (7m): 86% yield, 94% ee
12) 2-Me (7n): 26% yield, 87% ee
graphic file with name nihms361777t18.jpg
7o
13) 75% yield, 93% ee
graphic file with name nihms361777t19.jpg
14) 4-F (7p): 78% yield, 93% ee
15) 3-F (7q): 76% yield, 92% ee
16) 2-F (7r): 35% yield, 92% ee
graphic file with name nihms361777t20.jpg
7s
17) 88% yield, 92% ee
graphic file with name nihms361777t21.jpg
18) R = Me (7t): 61% yield, 85% ee
19) R = n-Bu (7u): 72% yield, 91% ee
20) R = i-Pr (7v): 66% yield, 92% ee
21) R = t-Bu (7w): 29% yield, 84% ee
graphic file with name nihms361777t22.jpg
7x
22) 80% yield, 90% ee
a

Reactions conducted under inert atmosphere on 0.1 or 0.2 mmol scale for 2 h. Isolated yields are reported. Enantiomeric excess was determined by chiral stationary phase SFC.

b

1.6 equiv SnCl4 were employed.